Article
Chemistry, Applied
Brigita Mudrakova, Peter Kisszekelyi, Denisa Vargova, Dorota Zakiewicz, Radovan Sebesta
Summary: This paper presents a highly enantio- and diastereoselective tandem transformation method, using Cu-catalyzed conjugate addition of Grignard reagents to heterocyclic Michael acceptors, followed by one-pot trapping of in situ formed enolates with stabilized carbocations or their equivalents. This method allows the installation of structurally attractive substituents on heterocyclic compounds.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Hyotaik Kang, Chao-Jun Li
Summary: This study presents the use of umpolung aldehydes as carbanion equivalents for highly regioselective 1,6-conjugate addition reactions to unsaturated ketones, with initial investigation into the enantioselective variant. It was found that the synergy of ruthenium(ii) catalyst and electron-rich, bidentate phosphine ligand is crucial for enhancing reactivity and selectivity under mild reaction conditions.
Article
Chemistry, Organic
Meng Li, Guang-Rui Peng, Xuan Yang, Zhen-Ning Ma, Jian-Bo Xie
Summary: We developed a copper-catalyzed enantio- and diastereoselective boron conjugate addition method for α-alkyl α,beta-unsaturated esters under base-free conditions. The approach exhibited excellent enantioselectivities and moderate to good conversions, although with moderate diastereoselectivities. The synthetic utility of this protocol was demonstrated.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Yong-Wang Huo, Xinxin Qi, Xiao-Feng Wu
Summary: This study developed a new method for synthesizing alpha,beta-unsaturated thioesters via nickel-catalyzed thiocarbonylation reaction of vinyl triflates with arylsulfonyl chlorides. By using Mo(CO)(6) as both CO source and reductant, alpha,beta-unsaturated thioesters were obtained in moderate to good yields with excellent functional group compatibility. It is notable that this is the first example of nickel-catalyzed carbonylative synthesis of alpha,beta-unsaturated thioesters using arylsulfonyl chlorides as the coupling partner.
Article
Chemistry, Multidisciplinary
Hu Tian, Hong-Ming Zhang, Liang Yin
Summary: In this article, a copper(I)-catalyzed asymmetric conjugate addition/protonation with selenols and alpha-substituted alpha,beta-unsaturated thioamides is described, which produces a series of chiral selenides with high to excellent enantioselectivity. The reaction shows a broad substrate scope for both selenols and alpha-substituted alpha,beta-unsaturated thioamides. The catalytic system is also successfully used for asymmetric selenation of beta-substituted alpha,beta-unsaturated thioamides. A [Cu-(R,R-P)-TANIAPHOS]-SePh species is identified by Se-77 NMR spectra, with a chemical shift at delta 462 ppm. Furthermore, a {[Cu-(R)-TOL-BINAP]-SePh}(2) species is characterized by X-ray analysis, confirming the formation of Cu-Se bond in the reaction. Finally, the straightforward transformations of the thioamide group to amine and thioester are demonstrated.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Daniel Rozsar, Alistair J. M. Farley, Iain McLauchlan, Benjamin D. A. Shennan, Ken Yamazaki, Darren J. Dixon
Summary: This article describes the enantioselective intermolecular conjugate addition of nitroalkanes to unactivated alpha,beta-unsaturated esters catalyzed by a bifunctional iminophosphorane (BIMP) superbase. It provides a straightforward approach to the synthesis of pharmaceutically relevant enantioenriched gamma-nitroesters with unprecedented selectivity. The methodology demonstrates broad substrate scope and has been successfully applied on a gram scale with reduced catalyst loading, allowing for catalyst recovery.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Leah J. Salituro, Jessica E. Pazienza, Scott D. Rychnovsky
Summary: This study reports the first total syntheses of strasseriolide A and B. Strasseriolide B exhibits potent activity against the wild-type malaria parasite Plasmodium falciparum and good activity against a chloroquine-resistant strain. A convergent strategy was employed, utilizing an aldehyde-acid fragment and a vinyl iodide-alcohol fragment, both prepared from chiral pool starting materials. The fragments were combined through a Yamaguchi esterification and cyclized with a Nozaki-Hiyama-Kishi reaction, resulting in the assembly of strasseriolide B in a 16-step LLS.
Article
Chemistry, Multidisciplinary
Wenjun Luo, Li-Ming Zhang, Zhan-Ming Zhang, Junliang Zhang
Summary: A novel family of PNP ligands (W-Phos) was designed and applied in the copper-catalyzed asymmetric addition of linear Grignard reagents to aryl alkyl ketones. This method allows for the facile synthesis of versatile chiral tertiary alcohols with high yields and excellent enantioselectivities. It also has the potential for the synthesis and modification of various densely functionalized medicinally relevant molecules.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Kohsuke Ohmatsu, Yusuke Morita, Mari Kiyokawa, Takashi Ooi
Summary: The stereoselective cyanoalkylation of electron-deficient olefins with potassium cyanide and alkyl halides was developed using modular chiral 1,2,3-triazolium salts as catalysts with hydrogen bond-donor ability. The reaction involves enantioselective conjugate addition of a cyanide ion and consecutive diastereoselective alkylation of intermediary chiral triazolium enolates controlled by the catalyst. Properly tuned chiral triazolium ion as a catalyst and the presence of cyano functionality in the enolate are crucial for achieving high levels of acyclic stereocontrol.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Won Jun Jang, Jeongkyu Woo, Jaesook Yun
Summary: The study reported a method to synthesize enantioenriched alkylboron compounds through conjugate addition, which are influenced by two contiguous carbon stereogenic centers, with high yield and enantioselectivity.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Christopher J. C. Cooze, Wesley McNutt, Markus D. Schoetz, Bohdan Sosunovych, Svetlana Grigoryan, Rylan J. Lundgren
Summary: Metal-catalyzed enantioselective conjugate additions are reliable methods for stereoselective synthesis, but multicomponent reactions initiated by conjugate arylation of acyclic pi-systems are rare. This study demonstrates a new Rh-catalyst system that allows highly enantioselective conjugate addition reactions of electron-deficient 1,3-dienes, generating Z-homoallylic alcohols with three stereocenters. The reaction products exhibit high diastereoselectivity and optical purity, enabling the synthesis of compounds with multiple stereocenters.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Organic
Hiroaki Shimizu, Kohei Yoshinaga, Satoshi Yokoshima
Summary: Treatment of ketones with a 2-nitrophenyl group at the alpha-position with sodium hydroxide in methanol at 60 degrees C leads to the formation of various nitrones. Unexpected isolation of N-hydroxyindolinone as a byproduct and proposed reaction mechanism involving an alpha-hydroxyketone. The resulting nitrones undergo inter- and intramolecular 1,3-dipolar cycloaddition with olefins to yield polycyclic isoxazolidines.
Article
Chemistry, Multidisciplinary
Jia-Ju Tao, Jia-Dong Tang, Tao Hong, Jia-Wen Ye, Jia-Yu Chen, Chunsong Xie, Zibin Zhang, Shijun Li
Summary: A new class of aza-crown ether-derived chiral BINOL catalysts showed higher enantioselectivity in the asymmetric Michael addition, although the host-guest complexation of alkali ions by the aza-crown ethers did not enhance the catalysis effectiveness. Chiral gamma,delta-unsaturated ketones were obtained in good enantioselectivities (81-95% ees) under mediation of the aza-crown ether-derived chiral BINOL and in the presence of a magnesium salt.
Article
Multidisciplinary Sciences
Shengtong Niu, Hao Zhang, Weici Xu, Prasanta Ray Bagdi, Guoxiang Zhang, Jinggong Liu, Shuang Yang, Xinqiang Fang
Summary: The article introduces the rationale, scope, and applications of the kinetic resolution of auxiliary adjacent alcohols (KRA*) strategy to overcome the challenges faced by contemporary asymmetric catalysis, allowing for the synthesis of optically enriched compounds with two, three, or four spatially and electronically similar groups.
NATURE COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Gleb A. Chesnokov, Karl Gademann
Summary: The marine-derived compound Peyssonnoside A was successfully synthesized for the first time in a concise, efficient, scalable, and highly diastereoselective manner. The aglucone peyssonnosol was achieved in 21% overall yield after 15 steps, with key reactions including Simmons-Smith cyclopropanation and Mukaiyama hydration controlled by the spatial structure of the substrates.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Pei Xu, Yi-Ming Zhu, Xin-Yu Liu, Xiao-Zhou Zhou, Shun-Yi Wang, Shun-Jun Ji
Summary: The study has developed a method for the synthesis of pyrroloisoquinoline derivatives through the formation of two C-C bonds and one C-N bond via radical cascade cyclization in one step.
CHINESE CHEMICAL LETTERS
(2021)
Article
Chemistry, Organic
Xin-Yu Liu, Shi-Yin Tian, Yi-Fan Jiang, Weidong Rao, Shun-Yi Wang
Summary: This study presents a visible-light-triggered radical cascade reaction for the trifunctionalization of butenyl benzothiazole sulfone derivatives under mild conditions.
Article
Chemistry, Organic
Ying Chen, Fei Wang, Bo-Xi Liu, Wei-Dong Rao, Shun-Yi Wang
Summary: A Ni(ii)-catalyzed reductive cross-coupling reaction has been developed for the synthesis of benzylic sulfides/selenides from oxalates and thiosulfonates/selenosulfonates under mild conditions. The use of oxalates prepared from corresponding alcohols as carbon radical precursors in the reaction provides an easy substrate availability and mild reaction conditions, offering a new method for the preparation of unsymmetrical sulfides/selenides with good functional group tolerance.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Multidisciplinary Sciences
Fei Wang, Ying Chen, Weidong Rao, Lutz Ackermann, Shun-Yi Wang
Summary: In this work, the authors present a new method for the synthesis of disulfides through a reductive nickel-catalyzed cross-electrophile coupling of unactivated alkyl bromides with symmetrical tetrasulfides, forming unsymmetrical disulfide intermediates. This approach offers practicality and scalability for disulfide synthesis.
NATURE COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Shi-Yin Tian, Jing-Jing Ai, Jia-Hui Han, Weidong Rao, Shu-Su Shen, Daopeng Sheng, Shun-Yi Wang
Summary: A photocatalytic synthesis method was developed to simultaneously construct two C-S/Se bonds and one C-C bond without the use of transition metals or other additives, using diphenyl disulfide or diphenyl diselenide as sulfur or selenium sources.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Zhenguo Zhang, Jun Gu, Yongheng Lv, Liang Ji, Xiaoxiao Liu, Beishen Wu, Fang Liu, Zhenhua Jia, Teck-Peng Loh
Summary: A metal-free synthesis of β-carbolines from tryptamines and aromatic aldehydes is achieved using a triaryl carbenium ion pair as a catalyst. This method exhibits excellent functional group tolerance and is demonstrated with the synthesis of Eudistomin U and fluorescent compounds on a large scale. Mechanistic studies reveal the formation of a trityl radical through a single-electron transfer process and its trapping by an oxygen molecule. In addition, an in-situ-generated reactive oxygen-centered radical is found to be essential for the efficient dehydroaromatization process.
CELL REPORTS PHYSICAL SCIENCE
(2023)
Article
Chemistry, Organic
Ying Chen, Fei Wang, Weidong Rao, Shusu Shen, Daopeng Sheng, Shun-Yi Wang
Summary: An efficient method for the copper-catalyzed ring-opening hydrolysis of silacyclobutanes to silanols was developed in this study. This strategy offers the advantages of friendly reaction conditions, simple operation, and good functional group compatibility. It also allows for the introduction of S-S bonds into organosilanol compounds in a single step. The successful gram scale synthesis demonstrates the potential of this protocol for practical industrial applications.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Letter
Chemistry, Organic
Yi-Fan Jiang, Wei-Chen Zhu, Xin-Yu Liu, Shi-Yin Tian, Jia-Hui Han, Weidong Rao, Shu-Su Shen, Daopeng Sheng, Shun-Yi Wang
Summary: Here, a new method is provided to synthesize 1,3-dibenzenesulfonylpolysulfane (DBSPS), which reacts with boronic acids to produce thiosulfonates. Commercially available boron compounds significantly expand the range of thiosulfonates. Experimental and theoretical investigations reveal that DBSPS can generate both thiosulfone and dithiosulfone fragments, with the latter being unstable and decomposing into thiosulfonates.
Article
Chemistry, Organic
Wang Chen, Xin-yu Liu, Daopeng Sheng, Yi-Fan Jiang, Weidong Rao, Shu-Su Shen, Zhao-Ying Yang, Shun-Yi Wang
Summary: A nickel-catalyzed C-SS reductive cross-coupling reaction for producing unsymmetric disulfides has been developed. This approach exhibits a broad substrate scope, excellent functional group tolerance, and can be conducted under mild conditions.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Jia-Hui Han, Shi-Yin Tian, Weidong Rao, Shu-Su Shen, Daopeng Sheng, Shun-Yi Wang
Summary: In this study, a visible-light-mediated selenylation/cyclization reaction using selenium radicals generated from diselenides as radical sources with acrylimide derivatives is described. This method provides a mild and effective approach for the synthesis of symmetrical selenosubstituted pyrrolidine-2,5-diones. The described catalytic strategy offers advantages such as mild reaction conditions, metal-free conditions, no additives required, easy operation, and a wide substrate range.
NEW JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Fei Wang, Ying Chen, Weidong Rao, Shu-Su Shen, Shun-Yi Wang
Summary: A Cu-catalyzed cascade reaction has been developed for the construction of S (Se)-containing organosilicon compounds using four-membered silacyclobutanes (SCBs) and thiosulfonates. The protocol exhibits a wide substrate scope, high functional group compatibility, and mild reaction conditions, enabling the formation of new C-S (Se) and Si-O bonds in a single step.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Ying Chen, Daopeng Sheng, Fei Wang, Weidong Rao, Shu-Su Shen, Shun-Yi Wang
Summary: A Ni(II)/TPMPP-catalyzed reductive cross-coupling reaction has been reported for the synthesis of unsymmetric disulfides from benzyl oxalates and tetrasulfides. This method offers mild reaction conditions, wide substrate range, and easy operation, and has successfully achieved gram-scale synthesis of disulfides.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Fei Wang, Ying Chen, Lutz Ackermann, Shun-Yi Wang
Summary: In this study, a selective cross-coupling reaction between unactivated alkyl bromides and diaryl tellurides was achieved using reductive nickel catalysis, leading to the synthesis of unsymmetrical alkyl-aryl tellurides with mild reaction conditions, high yields, easily accessible substrates, and a broad substrate scope.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Bo-Xi Liu, Fei Wang, Ying Chen, Wei-Dong Rao, Shu-Su Shen, Shun-Yi Wang
Summary: A visible-light-promoted regioselective denitrogenative cross-coupling between benzotriazinones and selenosulfonates has been developed for the synthesis of ortho-selenylated benzamides. The reaction provides good yields and demonstrates a general substrate scope. Furthermore, this protocol has been successfully employed for the one-pot two-step synthesis of a series of ebselen and its analogs.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Fei Wang, Shun-Yi Wang
Summary: The visible-light-promoted free radical cross-coupling method facilitates the efficient construction of unsymmetrical alkyl-alkyl selenide compounds under mild metal-free conditions, providing a green and simple approach with a wide substrate scope, high yields, and easy operation. Additionally, this strategy can also be applied for the efficient synthesis of aryl-alkyl selenides, heteroaryl-alkyl selenides, and aryl-alkyl sulfides.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Review
Chemistry, Multidisciplinary
Dan He, Yawen Li, Fuwen Zhao, Yuze Lin
Summary: High trap density in organic solar cells leads to localized charge carriers and reduced carrier lifetime, limiting device efficiency. This feature article summarizes the recent advances of trap suppression by material design and device engineering.
CHEMICAL COMMUNICATIONS
(2024)
Review
Chemistry, Multidisciplinary
Olivier Monfort, Arshitha Madhusudhan, Martin Motola
Summary: This article presents the advantages of coupling photocatalysis and Fenton-based processes for environmental remediation and discusses their synergy. It critically examines the simultaneous triggering of these two processes and provides insights into research approaches. The study aims to enhance understanding of this complex process and highlight the potential integration of new catalysts in current wastewater treatment technology.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Manideepa Dhar, Chittaranjan Mishra, Avijit Das, Uttam Manna
Summary: An approach of 'polymerization of monomers in its aggregated form' has been introduced to tailor the water wettability of fibrous and porous substrates, achieving hydrophobicity to superhydrophobicity transition, as well as patterned wettability. This facile chemical method provides a durable coating with adjustable and patterned wettability for various potential applications.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Saswat Ranjan Bhoi, Chhanda Debnath, Shikha Gandhi
Summary: In this article, a novel catalytic reaction using Pd(0) and Bronsted acid is reported for the synthesis of biologically important imidazolidinone-fused N-heterocycles through redox-neutral intramolecular N-allylation of indoles and pyrroles with alkynes. This atom-economical method is applicable to a wide range of substrates and eliminates the need for leaving groups or oxidizing agents commonly used in traditional allylation reactions.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Longkun Chen, Mingshuai Zhang, Meichen Liu, Zhuoyuan Liu, Yuetong Qiu, Zhilai Zhang, Fuchao Yu, Jiuzhong Huang
Summary: In this study, an efficient Rh(III)-catalyzed selective mono- and dual-C-H bond functionalization/cyclization with iodonium ylide as the sole coupling partner was demonstrated. Fused benzodiazepine skeletons were obtained in excellent yields, providing an improved approach to dual C-H unsymmetrical functionalization.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Alice Kennett, Sven Epple, Gabriella van der Valk, Irene Georgiou, Evelyne Gout, Romain R. Vives, Angela J. Russell
Summary: This study presents the design and synthesis of sulfated disaccharide inhibitors based on IdoA(2S)-GlcNS(6S), which showed potent inhibition of Sulf-2. The results suggest that IdoA(2S)-GlcNS(6S) is the shortest fragment size required for effective inhibition of Sulfs, and a trisulfated disaccharide is identified as the minimal fragment size of heparan sulfate for effective endosulfatase inhibition.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Mauro Garbini, Andrea Brunetti, Riccardo Pedrazzani, Magda Monari, Massimo Marcaccio, Giulio Bertuzzi, Marco Bandini
Summary: The self-adaptability of galvanostatic electrolysis was found to be helpful in a multistage chemo- and diastereoselective electrochemically promoted cyclodimerization of chalcones. Through a series of reductive events, densely functionalized cyclopentanes with five contiguous stereocenters were obtained (25 examples, yields up to 95%, dr values up to >20:1). Further experimental and electrochemical investigations indicated the crucial role of dynamic kinetic resolution of the aldol intermediate in the reaction mechanism.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Dhananjay S. Nipate, Neha Meena, Prakash N. Swami, Krishnan Rangan, Anil Kumar
Summary: In this study, the synthesis of functionalized benzo[a]phenazines and indazolo[2,3-a]quinolines was achieved through Rh(III)-catalyzed oxidative annulation of 2-arylquinoxalines and 2-aryl-2H-indazoles with allyl alcohols. The method showed a wide substrate scope, excellent functional group tolerance, good to high yields of annulated products, and the capability for scaled-up synthesis. A tentative mechanism of the annulation reaction was proposed based on a preliminary mechanistic investigation.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Ruonan Zhang, Abudukadi Tudi, Xia Yang, Xuping Wang, Zhihua Yang, Shujuan Han, Shilie Pan
Summary: A new lead tellurium borate material with a unique fundamental building block [B4O10] was synthesized and found to exhibit high birefringence. The structure-property relationship was discussed using first-principles calculations.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Amresh Kumar Singh, Baishali Thakurta, Anupam Giri, Monalisa Pal
Summary: This study introduces three key concepts for the quick synthesis of large-scale high-quality 2D materials films and their utilization in device fabrication.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Reina Hagiwara, Shun Nishimura, Kosuke Okeyoshi
Summary: A copolymer-conjugated nanocatalytic system has been developed to improve electron transfer and enhance photoinduced H2 generation.
CHEMICAL COMMUNICATIONS
(2024)